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Apronal
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Apronal
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Welcome to the community hub built on top of the Apronal Wikipedia article. Here, you can discuss, collect, and organize anything related to Apronal. The purpose of the hub is to connect people, foster de...
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Apronal
Apronal
Above: molecular structure of apronal Below: 3D representation of an apronal molecule
Clinical data
Routes of
administration
Oral
ATC code
Pharmacokinetic data
ExcretionRenal
Identifiers
  • (±)-N-Carbamoyl-2-propan-2-ylpent-4-enamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.677 Edit this at Wikidata
Chemical and physical data
FormulaC9H16N2O2
Molar mass184.239 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • O=C(NC(=O)N)C(C(C)C)C\C=C
  • InChI=1S/C9H16N2O2/c1-4-5-7(6(2)3)8(12)11-9(10)13/h4,6-7H,1,5H2,2-3H3,(H3,10,11,12,13) checkY
  • Key:KSUUMAWCGDNLFK-UHFFFAOYSA-N checkY
  (verify)

Apronal (brand name Sedormid), or apronalide, also known as allylisopropylacetylurea or allylisopropylacetylcarbamide, is a hypnotic/sedative drug of the ureide (acylurea) group synthesized in 1926[1] by Hoffmann-La Roche. Though it is not a barbiturate, apronal is similar in structure to the barbiturates (being an open-chain carbamide instead of having a heterocyclic ring).[2] In accordance, it is similar in action to the barbiturates, although considerably milder in comparison (formerly used as a daytime sedative at doses of 1 to 2 grams every 3 to 4 hours).[2] Upon the finding that it caused patients to develop thrombocytopenic purpura, apronal was withdrawn from clinical use.[3]

Medicines with apronal are no longer used except in Japan.[3] Notably Australian Therapeutic Goods Administration issued a safety alert in May 2023 which prohibits the sale, supply and use of Japanese EVE-branded products in Australia[4] due to its dangerous side effects.

See also

[edit]

References

[edit]
  1. ^ DE 459903, "Verfahren zur Darstellung von Ureiden der Dialkylessigsaeuren", issued 15 May 1928, assigned to Hoffmann-La Roche 
  2. ^ a b Roche Review ... Hoffman-La Roche, and Roche-organon. 1938. p. 164.
  3. ^ a b Vollum RL, Jamison DG, Cummins CS (20 May 2014). Fairbrother's Textbook of Bacteriology. Elsevier Science. pp. 152–. ISBN 978-1-4831-4178-7.
  4. ^ "EVE Apronal tablets". Therapeutic Goods Administration (TGA). Retrieved 31 May 2023.